Methanol → 3-Amino-1-phenylcyclopentanol

HRID 2404389Notes

Reaction equation

HRID 2404389 reaction equation
[OH:1][C:2]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:6][CH2:5][CH:4]([N:7]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:3]1.CO.O.NN>CC(OC)(C)C.O>[NH2:7][CH:4]1[CH2:5][CH2:6][C:2]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([OH:1])[CH2:3]1

Participants

6

Reactant 3

HCID 887MethanolHCID 24654Hydrazine hydrate (1:1)HCID 683134682-(3-Hydroxy-3-phenylcyclopentyl)isoindoline-1,3-dione

Product 1

HCID 683132843-Amino-1-phenylcyclopentanolYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

A solution of Example 58B (107 mg, 0.348 mmol), MeOH (5.5 mL), and hydrazine monohydrate (0.424 mL, 8.70 mmol) was heated at 50° C. for 1 hour, cooled to ambient temperature, and diluted with MTBE (50 mL) and water (25 mL). The layers were separated. The organic layer was washed with water (10 mL) and brine (10 mL), dried (Na2SO4), and concentrated to provide the title compound (34 mg, 0.19 mmol, 55% yield).

Workup

  1. customThe layers were separated
  2. washThe organic layer was washed with water (10 mL) and brine (10 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d9587df7c4ad41a893f1a40b825c456b
Source dataset
uspto-grants-2014_08
Patent number
US08802711B2

Reaction notes

Loading…